ꢀꢀꢀꢁ
934ꢀ ꢀJ. Safaei-Ghomi et al.: Nano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes
CDCl3): δ (ppm)ꢀ=ꢀ32.7, 41.6, 63.4, 123.9, 130.1, 147.2, 150.2, δ (ppm)ꢀ=ꢀ2.66 (dd, Jꢀ=ꢀ6, 15 Hz, 2H), 3.56–3.63 (m, 4H),
171.6. – Analysis for C20H18N4O6S2: calcd. C 50.62, H 3.82, N 3.82 (dd, Jꢀ=ꢀ1.6, 16 Hz, 2H), 5.72 (d, Jꢀ=ꢀ1.4 Hz, 2H), 7.31 (d,
11.81, S 13.51; found C 50.52, H 3.75, N 11.67, S 13.47.
Jꢀ=ꢀ5 Hz, 4H), 8.51 (d, Jꢀ=ꢀ5 Hz, 4H); 13C NMR (100 MHz, [D6]
DMSO): δ (ppm)ꢀ=ꢀ32.2, 40.3, 61.7, 121.1, 148.7, 149.8, 171.4.
– Analysis for C18H18N4O2S2: calcd. C 55.94, H 4.69, N 14.50,
S 16.59; found C 55.93, H 4.74, N 14.53, S 16.53.
4.5.5 3,3′-(Ethane-1,2-diyl)bis(2-(3-nitrophenyl)
thiazolidin-4-one) (4e) [12]
4.5.9 3,3′-(Ethane-1,2-diyl)bis(2-(p-tolyl)thiazolidin-4-
Cream solid, yield: 89%, m.p.: 222–224°C. – IR (KBr):
one) (4i) [12]
1
νꢀ=ꢀ2932, 1663, 1516 cm−1. – H NMR (400 MHz, [D6]DMSO):
δ (ppm)ꢀ=ꢀ2.63–2.69 (m, 2H), 3.53–3.59 (m, 2H), 3.62–3.68 (m,
2H), 3.88 (dd, Jꢀ=ꢀ1.7, 15 Hz, 2H), 5.95 (d, Jꢀ=ꢀ1.9 Hz, 2H), 7.53–
White solid, yield: 81%, m.p.: 158–160°C. – IR (KBr):
1
νꢀ=ꢀ2929, 1669 cm−1. – H NMR (400 MHz, CDCl3): δ
13
7.72 (m, 4H), 8.01–8.09 (m, 4H). – C NMR (100 MHz, [D6]
(ppm)ꢀ=ꢀ2.28 (s, 6H), 2.68–2.75 (m, 2H), 3.53–3.61 (m, 4H),
3.67 (dd, Jꢀ=ꢀ1.8, 16 Hz, 2H), 5.46 (d, Jꢀ=ꢀ1.5 Hz, 2H), 7.11 (s,
8H). – 13C NMR (100 MHz, CDCl3): δ (ppm)ꢀ=ꢀ20.8, 32.1,
39.5, 63.2, 126.7, 129.3, 135.3, 138.9, 171.1. – Analysis for
C22H24N2O2S2: calcd. C 64.05, H 5.86, N 6.79, S 15.54; found C
63.91, H 5.94, N 6.88, S 15.38.
DMSO): δ (ppm)ꢀ=ꢀ32.4, 41.4, 63.1, 126.2, 129.4, 130.8, 134.1,
143.9, 148.4, 171.5. – Analysis for C20H18N4O6S2: calcd. C 50.62,
H 3.82, N 11.81, S 13.51; found C 50.53, H 3.67, N 11.78, S 13.42.
4.5.6 3,3′-(Ethane-1,2-diyl)bis(2-(pyridin-2-yl)
thiazolidin-4-one) (4f) [30]
4.5.10 3,3′-(Ethane-1,2-diyl)bis(2-(4-isopropylphenyl)
Cream solid, yield: 88%, m.p.: 170–172°C. – IR (KBr):
νꢀ=ꢀ2937, 1674 cm−1. – 1H NMR (400 MHz, CDCl3): δ
thiazolidin-4-one) (4j) [12]
(ppm)ꢀ=ꢀ2.66 (dd, Jꢀ=ꢀ8, 18 Hz, 2H), 3.53–3.59 (m, 2H), 3.73– White solid, yield: 75%, m.p.: 163–165°C. – IR (KBr):
3.8 (m, 2H), 3.9 (dd, Jꢀ=ꢀ8, 18 Hz, 2H), 5.81 (d, Jꢀ=ꢀ1.2 Hz, 2H), νꢀ=ꢀ2955, 1661 cm−1. – 1H NMR (400 MHz, CDCl3): δ
7.17 (dd, Jꢀ=ꢀ5, 8 Hz, 2H), 7.2 (d, Jꢀ=ꢀ10 Hz, 2H), 7.62 (ddd, Jꢀ=ꢀ2, (ppm)ꢀ=ꢀ1.17 (d, Jꢀ=ꢀ7 Hz, 12H), 2.69–2.78 (m, 2H), 2.8–2.89
13
8, 10 Hz, 2H), 8.49 (d, Jꢀ=ꢀ5 Hz, 2H). – C NMR (100 MHz, (m, 2H), 3.55–3.64 (m, 4H), 3.68 (dd, Jꢀ=ꢀ1.8, 16 Hz, 2H), 5.48
CDCl3): δ (ppm)ꢀ=ꢀ32.9, 40.1, 63.3, 121.1, 123.5, 138.1, 150.5, (d, Jꢀ=ꢀ1.4 Hz, 2H), 7.13 (d, Jꢀ=ꢀ8 Hz, 4H), 7.16 (d, Jꢀ=ꢀ8 Hz,
158.4, 171.5. – Analysis for C18H18N4O2S2: calcd. C 55.94, H 4H). – 13C NMR (100 MHz, CDCl3): δ (ppm)ꢀ=ꢀ23.4, 32.2, 33.4,
4.69, N 14.50, S 16.59; found C 55.83, H 4.75, N 14.40, S 16.77. 39.6, 63.1, 126.67, 126.75, 135.6, 149.8, 171.1. – Analysis for
C26H32N2O2S2: calcd. C 66.63, H 6.88, N 5.98, S 13.68; found
C 66.46, H 6.79, N 6.05, S 13.53.
4.5.7 3,3′-(Ethane-1,2-diyl)bis(2-(pyridin-3-yl)
thiazolidin-4-one) (4g) [30]
5 Supplementary information
White solid, yield: 86%, m.p.: 195–197°C. – IR (KBr):
1
νꢀ=ꢀ2931, 1668 cm−1. – H NMR (400 MHz, [D6]DMSO): δ
NMR spectra of the products and other supporting data
(ppm)ꢀ=ꢀ2.68 (dd, Jꢀ=ꢀ6 Hz, 15, 2H), 3.49 (dd, Jꢀ=ꢀ6, 15 Hz, 2H),
3.62 (d, Jꢀ=ꢀ16 Hz, 2H), 3.9 (dd, Jꢀ=ꢀ1.9, 16 Hz, 2H), 5.78 (d,
Jꢀ=ꢀ1.7 Hz, 2H), 7.35–7.41 (m, 2H), 7.75–7.81 (m, 2H), 8.51–8.58
13
(m, 4H). – C NMR (100 MHz, [D6]DMSO): δ (ppm)ꢀ=ꢀ32.1,
Acknowledgment: The authors are grateful to University of
Kashan for supporting this work by Grant No.: 159196/XXI.
39.6, 61.4, 130.2, 134.8, 135.1, 148.5, 150.2, 171.1. – Analysis
for C18H18N4O2S2: calcd. C 55.94, H 4.69, N 14.50, S 16.59;
found C 55.81, H 4.74, N 14.40, S 16.65.
References
4.5.8 3,3′-(Ethane-1,2-diyl)bis(2-(pyridin-4-yl)
thiazolidin-4-one) (4h) [30]
[1] K. Appalanaidu, R. Kotcherlakota, T. L. Dadmal, V. S. Bollu, R. M.
Kumbhare, C. R. Patra, Bioorg. Med. Chem. Lett. 2016, 26, 5361.
White solid, yield: 84%, m.p.: 221–223°C. – IR (KBr):
[2] V. Ravichandran, A. Jain, K. S. Kumar, H. Rajak, R. K. Agrawal,
1
νꢀ=ꢀ2934, 1667 cm−1. – H NMR (400 MHz, [D6]DMSO):
Chem. Biol. Drug. Des. 2011, 78, 464.
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